Acaricide

ABSTRACT

An acaricide which contains as an effective ingredient an oxazoline or thiazoline compound represented by the following formula ##STR1## wherein, R 1 , R 2 , R 3 , R 4 , Z and A are as defined in the description. 
     This acaricide has an excellent acaricidal activity against house dust mites and mites and ticks which parasitize pets or wild animals or birds.

This application is a 371 of PCT/JP93/00783 filed Jun. 11, 1993.

This application is a 371 of PCT/JP93/00783 filed Jun. 11, 1993.

TECHNICAL FIELD

This invention relates to an agent for control of mites and ticks as an environmental pest, and specifically relates to an acaricide which contains an oxazoline or thiazoline compound as an effective ingredient, and displays an excellent control effect against house dust mites and mites and ticks which parasitize pets or wild animals or birds.

BACKGROUND ART

Oxazoline or thiazoline compounds, which mainly target mites which parasitize crops, are disclosed in Japanese Laid-Open Patent Publication Nos. 85268/1990 and 23287/1991. However, there is no disclosure in the above publications about control effect on mites which live in houses or mites which parasitize large or small animals or birds, etc.

Under the above circumstances, the object of this invention lies in developing a new use of some particular compounds among compounds which conceptionally included in the above official gazettes, and searching compounds capable of displaying an excellent control effect against mites as an environmental pest among the selected compounds.

DISCLOSURE OF INVENTION

The present inventors, for the purpose of fulfilling the above requisites, tested novel compounds invented as an agricultural acaricide on dust mites in houses and mites and ticks which parasitize livestock, and as a result found that these compounds show an extremely excellent acaricidal effect against them.

Namely, this invention is an acaricide, which contains as an effective ingredient an oxazoline or thiazoline compound represented by the following formula ##STR2## wherein, R¹ and R² are the same or different, and each denote a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a nitro group, a trifluoromethyl group or a trifluoromethoxy group,

R³ and R⁴ each denote a hydrogen atom, a halogen atom, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkylthio group having 1 to 20 carbon atoms, a lower alkoxy-lower alkyl group, a lower alkoxy-lower alkoxy group, an alkenyloxy group having 3 or more carbon atoms, a lower alkynyloxy group, a tri(lower alkyl)silyl group, a cycloalkyl group optionally substituted with a lower alkyl group or a group ##STR3## B denotes a direct bond, an oxygen atom, a lower alkylene group, a lower alkyleneoxy group, a lower alkylenedioxy group or a di(lower alkyl)silyl group,

Q denotes CH or a nitrogen atom,

n denotes an integer of 0 to 5,

R⁵ substituents, whose number is n, are the same or different, and each denote a halogen atom, a lower alkyl group, a lower alkoxy group, a lower haloalkyl group, a lower haloalkoxy group or a tri(lower alkyl)silyl group,

A denotes a direct bond or a lower alkylene group, and

Z denotes an oxygen atom or a sulfur atom.

In the present description, the term "lower" means that the number of carbon atoms of a group or compound to which this term was attached is 6 or less. The "halogen atom" denotes a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; the "alkyl group" denotes a straight-chain or branched alkyl group having 1 to 20, preferably 1 to 15 carbon atoms; the "alkoxy group" and the "alkylthio group" respectively denote an (alkyl)-O-group and an (alkyl)-S-group whose respective alkyl parts have the above meaning; and the "haloalkyl group" denotes an alkyl group at least one of whose hydrogen atoms bound to the carbon atoms is replaced with a halogen atom, such as, for example, chloromethyl, trifluoromethyl or trifluoroethyl. The "haloalkoxy group" denotes a (haloalkyl)-O-group wherein the haloalkyl part has the above meaning, such as, for example, a trifluoromethoxy group; and the "lower alkoxy-lower alkyl group" is a (lower alkyl)-O-(lower alkyl) group wherein each alkyl part has the above meaning, and includes, for example, ethoxymethyl, n-propoxymethyl, isopropoxymethyl, n-butoxymethyl, isobutoxymethyl, 2-methoxyethyl, 2-ethoxyethyl groups, etc.

The "lower alkoxy-lower alkoxy group" is a (lower alkyl)-O-(lower alkyl)-O-group wherein each alkyl part has the above meaning, and includes, for example, 2-methoxy-ethoxy, 2-ethoxyethoxy, 2-n-propoxyethoxy, 4-isopropoxybutoxy groups, etc. The "alkenyloxy group" is an alkenyl group whose alkenyl part is straight-chain or branched chain, and denotes an alkenyloxy group having 3 to 15 carbon atoms such as, for example, an allyloxy, butenyloxy, 3-methyl-2-butenyloxy, geranyloxy, farnesyloxy or citronellyloxy group; and as the "lower alkynyloxy group" can, for example, be exemplified a propargyloxy group. The "tri(lower alkyl)silyl group" includes, for example, trimethylsilyl, ethyldimethylsilyl, n-propyldi-methylsilyl, t-butyldimethylsilyl, triethylsilyl, methyldiethylsilyl groups, etc.

The "cycloalkyl group" includes those having 3 to 8 carbon atoms, e.g. a cyclohexyl group, and this cycloalkyl group may optionally be substituted with lower alkyl group(s). As examples of the thus substituted cycloalkyl groups can be mentioned methylcyclohexyl, ethylcyclohexyl, t-butylcyclohexyl groups, etc. The "lower alkylene group" denotes a straight-chain or branched chain alkylene group having 1 to 6 carbon atoms, and includes, for example, methylene, ethylene, propylene, butylene, 1,1-dimethylmethylene, etc. The "lower alkyleneoxy group" and the "lower alkylenedioxy group" are a-(lower alkylene)-O-group or -O-(lower alkylene)-group and an -O-(lower alkylene)-O- group, respectively, wherein each alkylene part has the above meaning. As example of the "di(lower alkyl)silyl group" can be mentioned dimethylsilyl, diethylsilyl, methylethylsilyl groups, etc.

Examples of the compounds of the formula (I) used in the invention are shown in the following Table 1 and Table 2.

The physical property value in the table denotes the refractive index (n_(D) ²⁵) or the melting point (°C.).

The abbreviations in the table mean the following meanings:

Me=Methyl, Et=Ethyl, Pr=Propyl,

Bu=Butyl, Ph=Phenyl

                                      TABLE 1                                      __________________________________________________________________________                                     Physical                                       Compound                        property                                       No.   R.sub.1, R.sub.2                                                                       Z R.sub.3, R.sub.4                                                                               value                                          __________________________________________________________________________     1     2-F     O H               57.0-60.0                                      2     2-Cl    O H               71.5-74.0                                      3     2-Br    O H               101.0-103.5                                    4     2-I     O H               1.6244                                         5     2,6-diCl                                                                               O H               1.5987                                         6     2-Cl, 4-NO.sub.2                                                                       O H               38.5-41.0                                      7     2-F     O 2-Cl            117.0-121.0                                    8     2-Cl    O 2-Cl            1.6093                                         9     2-Br    O 2-Cl            53.0-55.0                                      10    2-Cl    O 3-Cl            1.6093                                         11    2-Cl    O 4-Cl            1.6075                                         12    2-Br    O 4-Cl            1.6072                                         13    2-Cl    O 2-Br            1.6213                                         14    2-Cl, 6-F                                                                              O 4-Cl            1.5814                                         15    2-Cl, 6-F                                                                              O 4-F             1.5654                                         16    2,6-diCl                                                                               O 4-Cl            52.5˜53.5                                17    2,6-diF O 4-Cl            1.5701                                         18    2,6-diF O 4-Br            67.5˜69.0                                19    2-Cl    O 4-CF.sub.3      107.0-119.0                                    20    2-Cl, 6-F                                                                              O 2-CF.sub.3      1.5335                                         21    2-Cl, 6-F                                                                              O 4-CF.sub.3      1.5326                                         22    2,6-diF O 4-CF.sub.3      73.0-77.0                                      23    2-Cl    O 4-OCF.sub.3     61.0-62.0                                      24    2,6-diF O 4-OCF.sub.3     61.5-64.5                                      25    2,6-diF O 2,4-diF         1.5452                                         26    2-Cl    O 2,4-diCl        117.0-129.5                                    27    4-OCF.sub.3                                                                            O 2,6-diF         76.0-77.5                                      28    2,6-diF O 2,4-diCl        66.0-67.0                                      29    2,6-diF O 3,4-diCl        86.5-88.0                                      30    2,6-diF O 2-F, 4-Cl       65.0˜67.0                                31    2-Cl, 6-F                                                                              O 3,5-diF         1.5502                                         32    2-Cl    O 4-OMe           1.5004                                         33    2-Cl, 6-F                                                                              O 4-OMe           77.5-82.5                                      34    2,6-diF O 4-SMe           1.5962                                         35    2,6-diF O 2-Me, 4-Cl      1.5691                                         36    2,6-diF O 2-Me, 4-n-Octyl 1.5349                                         37    2,6-diF O 3-Cl, 4-Me      1.5695                                         38    2-Cl, 6-F                                                                              O 3-Br, 4-OMe     1.5892                                         39    2,6-diF O 2-OMe, 4-t-Bu   76.0-77.5                                      40    2,6-diF O 2-OMe, 4-n-Octyl                                                                               1.5356                                         41    2,6-diF O 2-OMe, 4-n-Nonyl                                                                               1.5329                                         42    2,6-diF O 2-OMe, 4-n-Decyl                                                                               1.5262                                         43    2,6-diF O 4-Et            1.5576                                         44    2,6-diF O 4-OEt           1.5578                                         45    2-Cl, 6-F                                                                              O 4-OEt           1.5719                                         46    2,6-diF O 2-OEt, 4-n-Nonyl                                                                               1.5264                                         47    2,6-diF O 2-OEt, 4-t-Bu   101.0-102.0                                    48    2-Cl, 6-F                                                                              O 2-OEt, 4-t-Bu   1.5500                                         49    2,6-diF O 2-OEt, 4-n-Octyl                                                                               1.5292                                         50    2-Cl, 6-F                                                                              O 2-F, 4-OEt      1.5870                                         51    2-Cl, 6-F                                                                              O 3-Cl, 4-OEt     83.0-85.0                                      52    2-Cl, 6-Cl                                                                             O 3-Br, 4-OEt     63.0-66.0                                      53    2,6-diF O 4-n-Pr          1.5474                                         54    2,6-diF O 4-i-Pr          1.5512                                         55    2,6-diF O 3-O-i-Pr        1.5504                                         56    2-Cl, 6-F                                                                              O 4-O-n-Pr        1.5631                                         57    2,6-diF O 4-O-i-Pr        1.5504                                         58    2-Cl, 6-F                                                                              O 4-O-i-Pr        1.5635                                         59    2,6-diF O 4-S-i-Pr        1.5758                                         60    2,6-diF O 2-O-n-Pr, 4-n-Pentyl                                                                           1.5362                                         61    2,6-diF O 2-O-n-Pr, 4-t-Bu                                                                               1.5349                                         62    2-Cl, 6-F                                                                              O 2-Cl, 4-O-i-Pr  1.5683                                         63    2,6-diF O 4-n-Bu          102.5-105.0                                    64    2,6-diF O 4-i-Bu          1.5447                                         65    2-Cl, 6-F                                                                              O 4-i-Bu          1.5558                                         66    2,6-diF O 4-sec-Bu        1.5974                                         67    2,6-diF O 4-t-Bu          1.5471                                         68    2-Cl, 6-F                                                                              O 4-t-Bu          1.5592                                         69    2,6-diMe                                                                               O 4-t-Bu          83.5-86.0                                      70    2,6-diF O 4-O-n-Bu        60.5-62.5                                      71    2-Cl, 6-F                                                                              O 4-O-n-Bu        55.0-56.0                                      72    2,6-diF O 4-O-i-Bu        1.5446                                         73    2,6-diF O 4-O-sec-Bu      1.5414                                         74    2,6-diF O 2-O-n-Bu, 4-t-Bu                                                                               1.5316                                         75    2,6-diF O 2-Cl, 4-t-Bu    1.5517                                         76    2,6-diF O 2-F, 4-O-n-Bu   1.5350                                         77    2,6-diF O 4-n-Pentyl      1.5445                                         78    2-Cl, 6-F                                                                              O 4-n-Pentyl      1.5527                                         79    2,6-diF O 4-i-Pr          68.0-71.0                                      80    2-Cl, 6-F                                                                              O 4-i-Pentyl      1.5504                                         81    2,6-diF O 4-t-Pentyl      1.5396                                         82    2-Cl, 6-F                                                                              O 4-neo-Pentyl    1.5543                                         83    2,6-diF O 4-O-n-Pentyl    1.5378                                         84    2,6-diF O 4-O-i-Pentyl    1.5396                                         85    2,6-diF O 2-O-n-Pentyl, 4-t-Bu                                                                           1.5280                                         86    2,6-diF O 2-F, 4-n-Pentyl 1.5274                                         87    2-Cl, 6-F                                                                              O 2-F, 4-n-Pentyl 1.5382                                         88    2,6-diF O 2-Cl, 4-n-Pentyl                                                                               1.5435                                         89    2,6-diF O 4-n-Hexyl       1.5531                                         90    2,6-diF O 4-i-Hexyl       1.5372                                         91    2-Cl, 6-F                                                                              O 4-i-Hexyl       1.5486                                         92    2,6-diF O 4-O-n-Hexyl     1.5350                                         93    2,6-diF O 2-O-n-Hexyl, 4-t-Bu                                                                            1.5398                                         94    2,6-diF O 2-F, 4-n-Hexyl  1.5272                                         95    2,6-diF O 2-Cl, 4-n-Hexyl 1.5440                                         96    2,6-diF O 4-n-Heptyl      1.5322                                         97    2-Cl, 6-F                                                                              O 4-n-Heptyl      1.5432                                         98    2,6-diF O 4-O-n-Heptyl    1.5314                                         99    2-Cl, 6-F                                                                              O 4-O-n-Heptyl    1.5419                                         100   2-Cl, 6-F                                                                              O 4-O--CH(di-n-Pr)                                                                               1.5401                                         101   2,6-diF O 2-F, 4-n-Heptyl 1.5236                                         102   2,6-diF O 2-Cl, 4-n-Hepyl 1.5406                                         103   2-CF.sub.3                                                                             O 4-n-Octyl       1.5166                                         104   2,6-diF O 4-n-Octyl       1.5226                                         105   2,6-diF O 4-O-n-Octyl     1.5292                                         106   2,6-diF O 2-F, 4-n-Octyl  1.5215                                         107   2-Cl, 6-F                                                                              O 2-F, 4-n-Octyl  1.5322                                         108   2,6-diF O 2-Cl, 4-n-Octyl 1.5372                                         109   2,6-diF O 4-n-Nonyl       1.5304                                         110   2-Cl, 6-F                                                                              O 4-n-Nonyl       1.5370                                         111   2,6-diF O 4-(1-Me-Octyl)  1.5294                                         112   2,6-diF O 4-O-n-Nonyl     1.5269                                         113   2,6-diF O 4-S-n-Nonyl     1.5512                                         114   2,6-diF O 2-F, 4-n-Nonyl  1.5184                                         115   2-Cl, 6-F                                                                              O 2-F, 4-n-Nonyl  1.5286                                         116   2,6-diF O 2-Cl, 4-n-Nonyl 1.5283                                         117   2-Cl, 6-F                                                                              O 4-O-(3,7-diMe-Octyl)                                                                           1.5377                                         118   2,6-diF O 4-n-Decyl       1.5241                                         119   2,6-diF O 4-O-n-Decyl     1.5236                                         120   2,6-diF O 2-n-Decyl, 4-F  1.5242                                         121   2,6-diF O 2-F, 4-n-Decyl  1.5154                                         122   2,6-diF O 2-Cl, 4-n-Decyl 1.5194                                         123   2,6-diF O 4-(4,8-diMe-Nonyl)                                                                             1.5315                                         124   2-Cl, 6-F                                                                              O 4-O-n-Undecyl   1.5310                                         125   2,6-diF O 2-F, 4-n-Undecyl                                                                               1.5150                                         126   2,6-diF O 4-n-Dodecyl     1.5194                                         127   2-Cl, 6-F                                                                              O 4-O-n-Dodecyl   1.5268                                         128   2,6-diF O 2-F, 4-n-Dodecyl                                                                               1.5106                                         129   2,6-diF O 4-O-n-Tridecyl  43.0-45.0                                      130   2,6-diF O 4-O-n-Tetradecyl                                                                               42.5-45.0                                      131   2,6-diF O 4-n-Pentadecyl  1.5352                                         132   2,6-diF O 4-O-n-Pentadecyl                                                                               53.5˜55.0                                133   2,6-diF O 4-O-n-Hexadecyl 66.0-70.0                                      134   2,6-diF O 4-O-n-Heptadecyl                                                                               59.0-60.5                                      135   2,6-diF O 4-O-n-Nonadecyl 61.0-61.5                                      136   2,6-diF O 4-O-n-Eicosyl   38.5-39.0                                      137   2-Cl, 6-F                                                                              O 4-CH.sub.2 -O-Et                                                                               1.5604                                         138   2,6-diF O 4-CH.sub.2 -O-i-pr                                                                             1.5340                                         139   2-Cl, 6-F                                                                              O 4-CH.sub.2 -O-i-Pr                                                                             1.5458                                         140   2,6-diF O 4-CH.sub.2 -O-i-Bu                                                                             1.5372                                         141   2,6-diF O 4-OEt-O-Et      1.5412                                         142   2,6-diF O 4-O-C.sub.4 H.sub.8 -O-i-Pr                                                                    1.5316                                         143   2-Cl, 6-F                                                                              O 4-O-Propargyl   1.5807                                         144   2,6-diF O 4-O-Geraniol    1.5482                                         145   2,6-diF O 4-O-β-Citronellol                                                                         1.5352                                         146   2,6-diF O 4-triMe-Silyl   1.5444                                         147   2-Cl, 6-F                                                                              O 4-triMe-Silyl   1.5556                                         148   2,6-diF O 4-triEt-Silyl   1.5444                                         149   2,6-diF O 4-t-Bu-diMe-Silyl                                                                              1.5413                                         150   2,6-diF O 4-Cyclohexyl    1.5586                                         151   2,6-diF O 4-Cyclohexyl(4-t-Bu)                                                                           1.5428                                         152   2-Cl, 6-F                                                                              O 4-Cyclohexyl(4-t-Bu)                                                                           1.5486                                         153   2,6-diF O 4-Ph             98.0-101.0                                    154   2-Cl, 4-F                                                                              O 4-Ph            88.0-92.0                                      155   2-Cl, 6-F                                                                              O 4-Ph(2-Cl)      1.6200                                         156   2,6-diF O 4-Ph(3-Cl)      66.5-67.5                                      157   2,6-diF O 4-Ph(4-Cl)      160.0-161.0                                    158   2-Cl, 6-F                                                                              O 4-Ph(4-Br)      101.0-102.0                                    159   2,6-diF O 4-Ph(2,4-diF)   1.5886                                         160   2,6-diF O 4-Ph(2-F, 4-Cl) 72.0-92.0                                      161   2-Cl, 6-F                                                                              O 4-Ph(2-F, 4-Cl) 77.0-95.0                                      162   2-Cl, 6-F                                                                              O 4-Ph(2-F, 4-Br) 1.6117                                         163   2,6-diF O 4-Ph(2-F, 4-Br) 1.5998                                         164   2-Cl    O 4-Ph(2,4-diCl)  1.6468                                         165   2,6-diF O 4-Ph(2,4-diCl)  1.6146                                         166   2,6-diF O 4-Ph(2-Cl, 4-Br)                                                                               1.6140                                         167   2,6-diF O 4-Ph(3,4-diCl)  114.0-115.0                                    168   2,6-diF O 4-Ph(3-Cl, 4-F)  98.5˜101.0                              169   2-F     O 4-Ph(4-OCF.sub.3)                                                                              79.0-85.0                                      170   2-Cl    O 4-Ph(4-OCF.sub.3)                                                                              65.0-66.5                                      171   2-CF.sub.3                                                                             O 4-Ph(4-OCF.sub.3)                                                                              74.0-76.0                                      172   2-OMe, 6-F                                                                             O 4-Ph(4-OCF.sub.3)                                                                              78.0-80.0                                      173   2,6-diF O 4-Ph(4-OCF.sub.3)                                                                              1.5900                                         174   2-Cl, 6-F                                                                              O 4-Ph(4-OCF.sub.3)                                                                              1.5990                                         175   2-Cl, 6-F                                                                              O 4-Ph(2-Cl, 4-OCF.sub.3)                                                                        1.5702                                         176   2,6-diF O 4-Ph(2-Br, 4-OCF.sub.3)                                                                        1.5840                                         177   2,6-diF O 4-Ph(4-O-CH.sub.2 --CF.sub.3)                                                                  128.0-131.5                                    178   2-Cl, 6-F                                                                              O 4-Ph(4-O-CH.sub.2 --CF.sub.3)                                                                  111.5-113.0                                    179   2,6-diF O 4-Ph(4-Me)      123.0-127.0                                    180   2,6-diF O 4-Ph(4-Et)      130.0-132.0                                    181   2-Cl, 6-F                                                                              O 4-Ph(4-OEt)     93.0-95.0                                      182   2,6-diF O 4-Ph(4-OEt)     91.0-92.0                                      183   2,6-diF O 4-Ph(4-n-Pr)    116.0-117.0                                    184   2,6-diF O 4-Ph(2-F, 4-n-Pr)                                                                              1.5854                                         185   2,6-diF O 4-Ph(2-Cl, 4-n-Pr)                                                                             1.5968                                         186   2,6-diF O 4-Ph(4-n-Bu)    95.0-96.0                                      187   2,6-diF O 4-Ph(4-i-Bu)    106.0-107.0                                    188   2,6-diF O 4-Ph(4-sec-Bu)  1.5939                                         189   2,6-diF O 4-Ph(2-F, 4-t-Bu)                                                                              1.5833                                         190   2,6-diF O 4-Ph(2-Me, 4-t-Bu)                                                                             1.5828                                         191   2,6-diF O 4-Ph(4-n-Pentyl)                                                                               60.0-62.0                                      192   2,6-diF O 4-Ph(4-i-Amyl)  79.0-80.0                                      193   2,6-diF O 4-Ph(2-F, 4-n-Pentyl)                                                                          69.5-71.0                                      194   2,6-diF O 4-Ph(4-n-Octyl) 65.0-67.5                                      195   2,6-diF O 4-Ph(4-triMe-Silyl)                                                                            1.5842                                         196   2-Cl, 6-F                                                                              O 3-F, 4-Ph       103.0-104.0                                    197   2,6-diF O 2-F, 4-Ph(4-Cl) 112.0-116.0                                    198   2-Cl, 6-F                                                                              O 2-F, 4-Ph(4-Cl) 1.6168                                         199   2,6-diF O 2-F, 4-Ph(2,4-diCl)                                                                            1.6062                                         200   2-Cl, 6-F                                                                              O 2-F, 4-Ph(2,4-diCl)                                                                            1.6101                                         201   2,6-diF O 2-F, 4-Ph(2-Me, 4-Cl)                                                                          1.5961                                         202   2,6-diF O 2-F, 4-Ph(4-Et)  99.5˜100.0                              203   2,6-diF O 2-F, 4-Ph(4-n-Pr)                                                                              1.5771                                         204   2,6-diF O 2-F, 4-Ph(4-i-Pr)                                                                              1.5961                                         205   2,6-diF O 2-F, 4-Ph(4-n-Pentyl)                                                                          66.5-67.0                                      206   2,6-diF O 2-F, 4-Ph(2-OEt, 4-t-Bu)                                                                       1.5722                                         207   2,6-diF O 2-F, 4-Ph(4-OCF.sub.3)                                                                         1.5656                                         208   2,6-diF O 2-Cl, 4-Ph(4-Cl)                                                                               1.6229                                         209   2,6-diF O 2-Cl, 4-Ph(4-n-Pr)                                                                             1.6005                                         210   2,6-diF O 2-Cl, 4-Ph(4-i-Pr)                                                                             1.6017                                         211   2,6-diF O 2-Cl, 4-Ph(4-t-Bu)                                                                             1.5900                                         212   2,6-diF O 2-Cl, 4-Ph(4-OCF.sub.3)                                                                        53.5-54.5                                      213   2,6-diF O 2-Me, 4-Ph(4-Et)                                                                               114.0-115.0                                    214   2,6-diF O 2-Me, 4-Ph(4-t-Bu)                                                                             1.5930                                         215   2,6-diF O 2-Me, 4-Ph(4-OCF.sub.3)                                                                        1.5648                                         216   2,6-diF O 2-Et, 4-Ph(4-OCF.sub.3)                                                                        1.5601                                         217   2,6-diF O 2-OMe, 4-Ph(4-OCF.sub.3)                                                                       1.5610                                         218   2-Cl, 6-F                                                                              O 2-OMe, 4-Ph(4-OCF.sub.3)                                                                       89.5-91.0                                      219   2,6-diF O 2-OMe, 4-Ph(4-n-Pr)                                                                            1.5852                                         220   2,6-diF O 2-OEt, 4-Ph(4-Cl)                                                                              1.6040                                         221   2,6-diF O 2-OEt, 4-Ph(4-OCF.sub.3)                                                                       1.5568                                         222   2,6-diF O 2-OEt, 4-Ph(4-i-Pr)                                                                            1.5830                                         223   2-Cl, 6-F                                                                              O 4-O-Pyridine    1.6034                                         224   2-Cl, 6-F                                                                              O 4-O-Pyridine(4-CF.sub.3)                                                                       89.0-89.5                                      225   2-Cl, 6-F                                                                              O 3-OPh           1.5995                                         226   2,6-diF O 4-OPh           1.5923                                         227   2-Cl, 6-F                                                                              O 4-OPh           1.6023                                         228   2-Cl, 4-NO.sub.2                                                                       O 4-OPh           85.0-88.0                                      229   2,6-diMe                                                                               O 4-OPh           1.6024                                         230   2-Cl, 6-F                                                                              O 4-OPh(4-Cl)     1.5573                                         231   2,6-diF O 4-OPh(4-Br)     1.5982                                         232   2-Cl, 6-F                                                                              O 4-OPh(4-Br)     1.6083                                         233   2,6-diF O 4-OPh(3-CF.sub.3)                                                                              1.5595                                         234   2,6-diF O 4-OPh(4-OCF.sub.3)                                                                             1.5437                                         235   2-Cl, 6-F                                                                              O 4-OPh(4-OCF.sub.3)                                                                             1.5542                                         236   2,6-diF O 4-OPh(2-Cl, 4-CF.sub.3)                                                                        1.5846                                         237   2-Cl, 6-F                                                                              O 4-OPh(2-Cl, 4-CF.sub.3                                                                         1.5918                                         238   2,6-diF O 4-OPh(4-Me)     1.5867                                         239   2-Cl, 6-F                                                                              O 4-OPh(4-Me)     1.5973                                         240   2,6-diF O 4-OPh(4-OMe)    1.5891                                         241   2-Cl, 6-F                                                                              O 4-OPh(4-OMe)    54.0-57.0                                      242   2-Cl, 6-F                                                                              O 4-OPh(4-n-Pr)   1.5861                                         243   2-Br    O 4-OPh(4-sec-Bu) 1.6046                                         244   2,6-diF O 4-OPh(4-sec-Bu) 1.5717                                         245   2-Cl, 6-F                                                                              O 4-OPh(4-t-Bu)   78.0-81.0                                      246   2,6-diF O 4-OPh(4-n-Hexyl)                                                                               1.5621                                         247   2,6-diF O 4-OPh(3,5-diMe, 4-O-n-Octyl)                                                                   1.5488                                         248   2,6-diF O 4-OPh(4-n-Dodecyl)                                                                             1.5387                                         249   2,6-diF O 4-OPh(4-O-n-Dodecyl)                                                                           43.0-44.0                                      250   2,6-diF O 2-F, 4-OPh(2-Cl, 4-CF.sub.3)                                                                   56.0-59.0                                      251   2-Cl, 6-F                                                                              O 3-Cl, 4-OPh(4-Cl)                                                                              1.6106                                         252   2-Cl, 6-F                                                                              O 3-Me, 4-OPh(4-Me)                                                                              1.5878                                         253   2,6-diF O 4-CH.sub.2 -Ph  1.5924                                         254   2-Cl, 6-F                                                                              O 4-CH.sub.2 -Ph  1.6004                                         255   2,6-diF O 4-CH.sub.2 -Ph(4-F)                                                                            1.5767                                         256   2,6-diF O 4-CH.sub.2 -Ph(4-Cl)                                                                           1.5920                                         257   2,6-diF O 4-CH.sub.2 -Ph(2,4-diF)                                                                        1.5719                                         258   2,6-diF O 4-CH.sub.2 -Ph(2,4-diCl)                                                                       1.5982                                         259   2-Cl, 6-F                                                                              O 4-CH.sub.2 -Ph(2,4-diCl)                                                                       1.6078                                         260   2,6-diF O 4-CH.sub.2 -Ph(2,3,4,5,6-penta-F)                                                              1.5494                                         261   2,6-diF O 4-CH.sub.2 -Ph(4-OCF.sub.3)                                                                    1.5617                                         262   2-Cl, 6-F                                                                              O 4-CH.sub.2 -Ph(4-OCF.sub.3                                                                     1.5722                                         263   2,6-diF O 4-CH.sub.2 -Ph(4-OMe)                                                                          1.5850                                         264   2,6-diF O 4-CH.sub.2 -Ph(4-Et)                                                                           1.5795                                         265   2,6-diF O 4-CH.sub.2 -Ph(4-i-Pr)                                                                         1.5824                                         266   2-Cl, 6-F                                                                              O 4-CH.sub.2 -Ph(4-i-Pr)                                                                         1.5956                                         267   2,6-diF O 4-CH.sub.2 -Ph(4-n-Bu)                                                                         1.5682                                         268   2-Cl, 6-F                                                                              O 4-CH.sub.2 -Ph(4-n-Bu)                                                                         1.5750                                         269   2-Cl, 6-F                                                                              O 4-CH.sub.2 -Ph(4-t-Bu)                                                                         1.5835                                         270   2,6-diF O 4-CH.sub.2 -Ph(4-n-Hexyl)                                                                      1.5585                                         271   2-Cl, 6-F                                                                              O 4-CH.sub.2 -Ph(4-n-Hexyl)                                                                      1.5702                                         272   2,6-diF O 4-CH.sub.2 -Ph(4-n-Octyl)                                                                      1.5514                                         273   2-Cl, 6-F                                                                              O 4-CH.sub.2 -Ph(4-n-Octyl)                                                                      1.5620                                         274   2,6-diF O 2-F, 4-CH.sub.2 -Ph(4-Cl)                                                                      1.5908                                         275   2,6-diF O 2-F, 4-CH.sub.2 -Ph(4-t-Bu)                                                                    1.5632                                         276   2,6-diF O 2-F, 4-CH.sub.2 -Ph(4-n-Octyl)                                                                 1.5464                                         277   2,6-diF O 2-Cl, 4-CH.sub.2 -Ph(4-n-Octyl)                                                                1.5474                                         278   2,6-diF O 4-C.sub.2 H.sub.4 -Ph(4-Cl)                                                                    1.5869                                         279   2-Cl, 6-F                                                                              O 4-C.sub.2 H.sub.4 -Ph(4-Cl)                                                                    1.5968                                         280   2-Cl, 6-F                                                                              O 4-CH(Me)-Ph(4-Et)                                                                              1.5706                                         281   2,6-diF O 4-CH(i-Bu)-Ph(4-Cl)                                                                            1.5768                                         282   2-Cl, 6-F                                                                              O 4-CH(i-Bu)-Ph(4-Cl)                                                                            1.5896                                         283   2,6-diF O 4-C(diMe)-Ph(4-Cl)                                                                             1.5493                                         284   2-Cl, 6-F                                                                              O 4-C(diMe)-Ph(4-n-Octyl)                                                                        1.5421                                         285   2,6-diF O 2-F, 4-C(diMe)-Ph(4-Cl)                                                                        1.5624                                         286   2,6-diF O 4-OCH.sub.2 -Ph 69.0-72.0                                      287   2-Cl, 6-F                                                                              O 4-OCH.sub.2 -Ph 1.5965                                         288   2,6-diF O 4-OCH.sub.2 -Ph(2-Cl)                                                                          1.5942                                         289   2-Cl, 6-F                                                                              O 4-OCH.sub.2 -Ph(2-Cl)                                                                          65.0-66.5                                      290   2,6-diF O 4-OCH.sub.2 -Ph(4-F)                                                                           106.0-107.0                                    291   2,6-diF O 4-OCH.sub.2 -Ph(4-Cl)                                                                          112.0-116.0                                    292   2-Cl, 6-F                                                                              O 4-OCH.sub.2 -Ph(4-Cl)                                                                          117.5-118.0                                    293   2,6-diF O 4-OCH.sub.2 -Ph(2,6-diF)                                                                       1.5632                                         294   2-Cl, 6-F                                                                              O 4-OCH.sub.2 -Ph(2,6-diF)                                                                       1.5742                                         295   2,6-diF O 4-OCH.sub.2 -Ph(2,3-diCl)                                                                      1.5936                                         296   2,6-diF O 4-OCH.sub.2 -Ph(3,4-diCl)                                                                      69.0-70.5                                      297   2-Cl, 6-F                                                                              O 4-OCH.sub.2 -Ph(3,4-diCl)                                                                      1.6049                                         298   2,6-diF O 4-OCH.sub.2 -Ph(3,5-diCl)                                                                      76.0-78.0                                      299   2,6-diF O 4-OCH.sub.2 -Ph(4-CF.sub.3)                                                                    106.5-108.5                                    300   2,6-diF O 4-OCH.sub.2 -Ph(4-OCF.sub.3)                                                                   94.5-97.0                                      301   2,6-diF O 4-OCH.sub.2 -Ph(4-Et)                                                                          105.0-106.5                                    302   2,6-diF O 4-OCH.sub.2 -Ph(4-i-Pr)                                                                        1.5741                                         303   2,6-diF O 4-OCH.sub.2 -Ph(4-t-Bu)                                                                        1.5649                                         304   2,6-diF O 4-OCH.sub.2 -Ph(4-n-Pentyl)                                                                    77.5-78.5                                      305   2,6-diF O 3-Me, 4-OCH.sub.2 -Ph(4-Et)                                                                    97.5˜99.5                                306   2-Cl, 6-F                                                                              O 4-CH.sub.2 -O-Ph(4-Cl)                                                                         111.0-113.0                                    307   2,6-diF O 4-O-C.sub.4 H.sub.8 -O-Ph(4-Cl)                                                                1.5678                                         308   2-Cl, 6-F                                                                              O 4-O-C.sub.4 H.sub.8 -O-Ph(4-Cl)                                                                1.5598                                         309   2,6-diF O 4-Silyl(diMe)-Ph                                                                               1.5778                                         310   2-OMe   S H               134.0-142.0                                    311   2,6-diF S 4-i-Pentyl      58.5-60.5                                      312   2,6-diF S 4-n-Octyl       1.5553                                         313   2,6-diF S 4-Ph(4-OCF.sub.3)                                                                              92.0-94.0                                      314   2,6-diF S 4-OPh(4-Me)     61.0-63.0                                      315   2-Cl, 6-F                                                                              S 4-CH.sub.2 -Ph(4-i-Pr)                                                                         57.0-65.0                                      316   2,6-diF S 2-F, 4-CH.sub.2 -Ph(4-Cl)                                                                      1.6166                                         __________________________________________________________________________

                  TABLE 2                                                          ______________________________________                                                                                Physical                                Compound                               property                                No.     R.sub.1, R.sub.2                                                                        Z      A      R.sub.3, R.sub.4                                                                       value                                   ______________________________________                                         317     2-Cl     O      --CH.sub.2 --                                                                         H       90.0-93.0                               318     2,6-diF  O      --CH.sub.2 --                                                                         4-n-Octyl                                                                              1.5274                                  319     2-Cl, 6-F                                                                               O      --CH.sub.2 --                                                                         4-n-Octyl                                                                              1.5354                                  320     2,6-diF  O      --CH.sub.2 --                                                                         4-Ph    1.6077                                  321     2-Cl     S      --CH.sub.2 --                                                                         3-Cl    68.5-71.0                               322     2-Br     S      --CH.sub.2 --                                                                         H       91.5-98.0                               323     2-OMe    S      --CH.sub.2 --                                                                         4-Me    1.6040                                  324     2-OMe    S      --CH.sub.2 --                                                                         3-Cl    1.6249                                  ______________________________________                                    

As apparent from the later-described test examples, the compounds of the above formula (I) provided by this invention have an extremely excellent acaricidal effect, and can be used as an acaricide for control of mites which externally parasitize the skins, etc. of animals (livestock, poultry, pets, wild animals, birds, etc.), control of mites which parasitize dwelling environment such as houses and offices, for example house dust mites, etc.

As specific examples of mites and ticks as the target can be mentioned Dermatophagoides farinae, Tyrophagus putrescentiae, Aieuroglyphus ovatus, Tarsonemus granarius, Haplochthonius simplex, Coamochthonius reticulalus, Ornithonyssus bacoti, Macrocheles muscaedomesticae, Rhipicephalus sanguineus, Haemaphysalis flava, Ixodes ovatus, Haemaphysalis longicornis, Haemaphysalis mageshimaensis, etc.

As to the acaricide of this invention, the compounds represented by the formula (I) can be used as such, but they are usually utilized after they are carried on liquid carriers, solid carriers or gaseous carriers, and then emulsifiers, dispersants, wetting agents, propellants, stabilizers, and other various auxiliaries are added according to necessity to make the mixtures into various forms fit for the application areas and the application methods, for example powders, granules, emulsions, oil solutions, aerosols, paints, fumigants, etc.

The liquid carriers include solvents such as xylene, toluene, benzene, cyclohexane, acetone, alcohols, mineral oils, petroleum and water.

The solid carriers include vegetable powders such as soybean meal and wheat flour, and mineral fine powders such as diatom earth, talc, kaolin, bentonite and clay.

The emulsifiers and dispersants include soaps, polyoxyethylene fatty alcohol ethers, polyoxyethylene fatty acid esters, sulfate esters of higher alcohols, alkylarylsulfonate salts, etc.

The propellants include, for example, liquefied petroleum gases, dimethyl ether, fluorocarbons, etc.

The acaricide of this invention can further contain various insecticides, synergists, pest repellents, antioxidants, stabilizers, bactericides, fungicides, perfumes, etc.

The amount of the effective ingredient in the acaricide of this invention can suitably be determined in accordance with its formulation form, application method and application place, but in the case of use in the form of liquid formulations such as wettable powders and emulsions, the amount can be 0.1 to 50.0% by weight, preferably 1.0 to 20.0% by weight. Further, in the case of use in the form of solids such as powders, the amount can be 0.1 to 50.0% by weight, preferably 2.0 to 20.0% by weight.

The acaricide of this invention can be applied externally to animals to be treated by a means such as application, atomization, pour-on, painting or immersion; or can be applied to places in dwelling environment such as houses and offices, where mites parasitize or may parasitize, for example carpets, tatami mats, places where indoor dust gathers, etc.

Its dose is an acaricidally effective amount, and cannot be sweepingly described because it largely varies depending on its application target, its application place, etc., but its optimal application amount may readily be determined by a person skilled in the art by carrying out a small-scale experiment. If an example is given as a tentative standard, the dose can be 0.01 g or more, preferably in the range of 0.05 to 1.0 g as the amount of the effective ingredient per m² of the area to be treated.

EXAMPLE

Formulation examples of compounds of this invention and test examples of acaricides of this invention are shown below. However, carriers, surfactants, etc. to be added in the formulations of the invention are not limited those used in these formulation examples.

Formulation Example 1 (powder)

2 parts of a compound of this invention (Compound No. 47), 50 parts of talc and 48 parts of clay are uniformly mixed and ground to give a powder.

Formulation Example 2 (wettable agent)

20 parts of a compound of this invention (Compound No. 104), 5 parts of sodium dodecylbenzenesulfonate, 3 parts of polyoxyethylene nonyl phenyl ether, 30 parts of clay and 42 parts of diatom earth are uniformly mixed and ground to give a wettable agent.

Formulation Example 3 (emulsion)

78 parts of xylol is added to 1.0 part of a compound of this invention (Compound No. 173) and 12 parts of polyoxyethylene nonyl phenyl ether, and the mixture is made into an emulsion where the solutes are uniformly dissolved.

Test Example 1

An acetone solution of a test compound was mixed with a feed so that the concentration of the test compound in the resultant treated feed became 1,000 ppm. 10 g of the treated feed was put in a 100-ml vial, Tyrophagus putrescentiae in the number of about 1,000 or Dermatophagoides farinae in the number of about 1,000 was inoculated thereon, and the vial was covered with a sheet of filter paper. Three weeks after the inoculation, the number of the living mites on the feed was counted about each kind of the mites according to the saline floating method. The effect of each of the chemicals tested was evaluated by calculating the proliferation rate according to the following equation; and grading the chemicals into 6 groups, namely grading rank A to a chemical among the above chemicals which gives a proliferation rate of 0 or more and under 5, grading rank B to a chemical which gives a proliferation rate of 5 or more and under 10, grading rank C to a chemical which gives a proliferation rate of 10 or more and under 20, grading rank D to a chemical which gives a proliferation rate of 20 or more and under 50, grading rank E to a chemical which gives a proliferation rate of 50 or more and under 90, and grading rank F to a chemical which gives a proliferation rate of 90 or more. The effect of rank A is the highest and the effect of rank F is the lowest.

    Proliferation rate(%)=C.sub.1 /C.sub.2 ×T.sub.2 /T.sub.1 ×100

C₁ : number of mites released in the untreated section

C₂ : number of living mites at the time of investigation in the untreated section

T₁ : number of mites released in the treated section

T₂ : number of living mites at the time of investigation in the treated section

As a result, high activities were observed, namely of B in respect of 1, 2, 4, 5, 7, 9, 10, 27, 37, 38, 134, 135, 136, 144, 228, 248, 310, 317, 320, 321, 322, 323 and 324 among the exemplified compounds (exemplified compound numbers 1 to 324), and of A in respect of all the other exemplified compounds.

Test Example 2

Eggs (about 50 eggs) of Haemaphysalis longicornis were placed on a sheet of filter paper treated with an acetone solution of a test compound so that the amount of the test compound became 500 μg/cm², and contacted with the sheet all day and night. The treated eggs were preserved in a 100-ml vial, and 5 weeks later hatch rates were investigated. ##EQU1##

As a result, all of the exemplified compounds (exemplified compound numbers 1 to 324) exhibited a high ovicidal effect of 90 to 100%. 

We claim:
 1. A method for control of ticks which externally parasitize pets or wild animals or birds, which method comprises applying an acaricidally effective amount of an oxazoline compound to the pets or wild animals or birds, said compound represented by the following formula ##STR4## wherein R³ denotes a fluorine atom, a chlorine atom, a C₁ to C₁₅ alkyl group or a C₁ to C₁₅ alkoxy group, and R² denotes a fluorine atom or a chlorine atom.
 2. A method according to claim 1 wherein R³ denotes a fluorine atom and R² denotes a fluorine atom.
 3. A method according to claim 1 wherein R³ denotes a methyl group and R² denotes a fluorine atom. 